US6326504B1 - Procedure to extract natural products - Google Patents
Procedure to extract natural products Download PDFInfo
- Publication number
- US6326504B1 US6326504B1 US09/154,030 US15403098A US6326504B1 US 6326504 B1 US6326504 B1 US 6326504B1 US 15403098 A US15403098 A US 15403098A US 6326504 B1 US6326504 B1 US 6326504B1
- Authority
- US
- United States
- Prior art keywords
- solvent
- extraction
- supercritical fluid
- vegetable
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/02—Medicinal preparations containing materials or reaction products thereof with undetermined constitution from inanimate materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/56—Materials from animals other than mammals
- A61K35/60—Fish, e.g. seahorses; Fish eggs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/75—Rutaceae (Rue family)
- A61K36/752—Citrus, e.g. lime, orange or lemon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
Definitions
- This invention relates to a procedure to extract organic products from vegetable or animal matrices, or their extracts, by means of high-pressure extraction using conventional liquid solvents and in the presence of small amounts of supercritical fluids.
- the present invention relates to a high pressure process for extraction of organic products from vegetable or animal matrices or extracts thereof wherein the process is carried out in the presence of one or more liquid solvents and one or more supercritical fluids wherein the proportion of the supercritical fluid is less than 50% by weight of the total weight of the solvent and the supercritical fluid.
- the process of the invention includes macerating the initial material at pressures of between 50 and 500 bar, in a solvent such as water, hydrocarbon, alcohol, ketone, ether, carbon halide or a mixture thereof, containing a supercritical fluid (SCF) such as CO 2 , propane, ethane or mixtures thereof in a proportion of less than 50% by weight of the total weight of the solvent and the SCF.
- a supercritical fluid such as CO 2 , propane, ethane or mixtures thereof in a proportion of less than 50% by weight of the total weight of the solvent and the SCF.
- the high working pressure causes the penetration of SCF, as it reduces its viscosity and increases diffusivity. This increase in diffusivity and reduction in viscosity causes the mobility of SCF through the inside of the cells and allows substances to be extracted at a much higher speed and in greater quantities than the conventional extractions or in other existing extraction patents to data.
- the extraction mechanism means that the product extracted by the SCF is solvated quickly with traditional solvent, setting a balance between solute-SCF-conventional solvent which allows extraction to be performed at all times with the same levels of effectiveness and performance as at the start of the process. There is a continuous transfer of matter from the cells to the conventional solvent, using an intermediate phase formed by the SCF.
- the innovation of the process over existing processes lies in the fact that proportions between SCF and conventional solvent are inverted, meaning that the resulting mixture is not an SCF but a pressure liquid or a mixture of phases.
- This process means that the main solvent is not an SCF but ethanol, water or other solvents, which are found in greater proportions.
- the SCF does not act as a solvent but as a transport vehicle between the vegetable matrix and the solvent.
- the procedure according to the invention minimizes extraction time, reduces the solvent/solute ratio and therefore reduces pumping costs, the consumption of solvent and costs for its later recuperation.
- the volume of the extractor is reduced for a certain production, or the production increases for a determined volume of extraction.
- This type of extraction can be applied to the extraction of organic products such as essential oils, dyes, alkaloids, lipids, oils, waxes, proteins, fatty acids, aromas, spices, isoprenoids, steroids, carotenes, or active pharmaceutical principles present in, or originating from extracts provided by the technique, such as oleoresin or adsorbate, or present in or originating from biological matrices, such as orange skin, paprika, grape skin, coffee, tea, medicinal plants, seeds, carrot or fish viscera.
- organic products such as essential oils, dyes, alkaloids, lipids, oils, waxes, proteins, fatty acids, aromas, spices, isoprenoids, steroids, carotenes, or active pharmaceutical principles present in, or originating from extracts provided by the technique, such as oleoresin or adsorbate, or present in or originating from biological matrices, such as orange skin, paprika, grape skin, coffee, tea, medicinal plants, seeds, carrot or fish viscera
- the solvents that can be used in the process of the invention are those solvents that are conventionally used to extract organic products from vegetable or animal matrices or extracts thereof.
- examples of such solvents include water, ethanol, and hexane.
- Preferred solvents are pentane, hexane, dichlorfluoromethane, chlorofuluromethane, dichloromethane, dimethylethere, ethylmethylether, diethylether, methanol, ethanol, acetone, ethyl butyl ketone, or mixtures thereof.
- Preferred SCF's include carbon dioxide, carbon anhydride, methane, ethane, propane, or mixtures thereof.
- the proportion of SCF to solvent less than 50% by weight based on the total weight of the SCF and solvent.
- the proportion of SCF to solvent is preferably between about 7 to about 35% by weight, most preferably about 11 to about 26 % by weight.
- the higher concentrations of SCF are preferred when the animal or vegetable matrix is porous or akin.
- the lower concentrations of SCF are preferred if the matrix is more compact and less porous.
- the process according to the invention is performed at pressures of between 50 and 500 bar, preferably between about 150 to about 280 bar.
- the time required to perform this operation is generally between about 0.25 and about 20 hours, preferably between about 0.5 and about 5 hours, most preferably between about 15 minutes and about 2 hours.
- the extraction temperature is typically less than 90° C., preferably between about 40° C. and about 80° C.
- the extracted product which is dissolved in the solvent is collected after depressurization.
- This technique can be combined with a separation phase which allows the extract to be recuperated or fractionated.
- This recuperation or fiactionation can be carried out following any process offered by the technique and known in the prior art.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Botany (AREA)
- Alternative & Traditional Medicine (AREA)
- Cell Biology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developmental Biology & Embryology (AREA)
- Immunology (AREA)
- Virology (AREA)
- Zoology (AREA)
- Marine Sciences & Fisheries (AREA)
- Extraction Or Liquid Replacement (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/ES1997/000015 WO1998032449A1 (es) | 1996-02-22 | 1997-01-28 | Procedimiento para extraer productos naturales mediante fluidos supercriticos |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES1997/000015 Continuation-In-Part WO1998032449A1 (es) | 1996-02-22 | 1997-01-28 | Procedimiento para extraer productos naturales mediante fluidos supercriticos |
Publications (1)
Publication Number | Publication Date |
---|---|
US6326504B1 true US6326504B1 (en) | 2001-12-04 |
Family
ID=8297787
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/154,030 Expired - Fee Related US6326504B1 (en) | 1997-01-28 | 1998-09-16 | Procedure to extract natural products |
Country Status (6)
Country | Link |
---|---|
US (1) | US6326504B1 (es) |
EP (1) | EP0917876B1 (es) |
AT (1) | ATE285242T1 (es) |
CA (1) | CA2250051A1 (es) |
DE (1) | DE69732031D1 (es) |
WO (1) | WO1998032449A1 (es) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030099565A1 (en) * | 2001-10-12 | 2003-05-29 | Korea Institute Of Science And Technology | Method for removing waxes from molded part in powder injection molding by using mixed fluid |
US6576273B2 (en) * | 2000-08-24 | 2003-06-10 | Chr. Hansen A/S | Purification process for improving total yield of curcuminoid colouring agent |
US20040026318A1 (en) * | 2000-06-22 | 2004-02-12 | Lemaire Benoit | Method for fractionating essential oils using at least a fluorinated solvent |
US20040131748A1 (en) * | 2002-11-12 | 2004-07-08 | Water Solutions, Inc. | Process for extracting carotenoids from fruit and vegetable processing waste |
US20040191384A1 (en) * | 2003-03-25 | 2004-09-30 | Naik Jarpla Pura | Process for the preparation of colorant from oleoresin |
US20060213533A1 (en) * | 1997-12-24 | 2006-09-28 | Imam Emami | Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters |
US20060252949A1 (en) * | 2003-09-25 | 2006-11-09 | Lalit Chordia | Recovery of residual specialty oil |
FR2905284A1 (fr) * | 2006-08-29 | 2008-03-07 | Nat Invo Sarl | Procede d'extraction d'une substance d'un materiau. |
US20080233238A1 (en) * | 2007-02-08 | 2008-09-25 | Grimmway Enterprises, Inc. | Supercritical co2 carrot feedstock extraction |
EP1986756A1 (en) * | 2006-02-07 | 2008-11-05 | Industrial Research Limited | Near-critical fluid extraction process |
US20110094961A1 (en) * | 2009-10-22 | 2011-04-28 | Epic Oil Extractors, Llc | Extraction of solute from solute-bearing material |
US20110112329A1 (en) * | 2009-11-11 | 2011-05-12 | Dynasep Llc | Energy efficient acetone drying method |
EP2428258A1 (en) * | 2010-05-31 | 2012-03-14 | China Agricultural University | Process for extracting plant-derived natural products with polarity or intermediate polarity |
US9132363B2 (en) | 2012-11-20 | 2015-09-15 | Apeks Llc | Extraction system |
US9908062B2 (en) | 2012-11-20 | 2018-03-06 | Andrew Paul Joseph | Extraction apparatus and method |
CN108288738A (zh) * | 2018-01-30 | 2018-07-17 | 常州大学 | 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITAN20030053A1 (it) * | 2003-10-08 | 2005-04-09 | Mauro Angeletti | Processo per la produzione di estratto da semi d'uva a basso contenuto di polifenoli monomerici |
BRPI0709379A2 (pt) * | 2006-03-17 | 2011-07-12 | Herbalscience Singapore Pte Ltd | extratos e métodos que compreendem espécies de cúrcuma |
CZ301511B6 (cs) * | 2008-06-25 | 2010-03-31 | Ceská geologická služba | Metoda na získávání vápnitých nebo pyritizovaných fosílií z vápnitých hornin |
CN112843776A (zh) * | 2020-12-24 | 2021-05-28 | 常州市芙丽佳生物科技有限公司 | 一种橄榄仁提取物的提纯工艺 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5110509A (en) | 1988-07-25 | 1992-05-05 | Siegfried K. Peter | Process for the recovery of monoglycerides and diglycerides from a mixture containing monoglycerides, diglycerides, and triglycerides |
US5210240A (en) * | 1984-08-09 | 1993-05-11 | Siegfried Peter | Process for the extraction of oil containing vegetable materials |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD294280A5 (de) * | 1990-05-11 | 1991-09-26 | Adw Institut Fuer Biotechnologie,De | Verfahren zur gewinnung von polyhydroxyfettsaeuren aus bakterienbiomasse |
-
1997
- 1997-01-28 EP EP97903387A patent/EP0917876B1/en not_active Expired - Lifetime
- 1997-01-28 DE DE69732031T patent/DE69732031D1/de not_active Expired - Fee Related
- 1997-01-28 CA CA002250051A patent/CA2250051A1/en not_active Abandoned
- 1997-01-28 AT AT97903387T patent/ATE285242T1/de not_active IP Right Cessation
- 1997-01-28 WO PCT/ES1997/000015 patent/WO1998032449A1/es active IP Right Grant
-
1998
- 1998-09-16 US US09/154,030 patent/US6326504B1/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5210240A (en) * | 1984-08-09 | 1993-05-11 | Siegfried Peter | Process for the extraction of oil containing vegetable materials |
US5110509A (en) | 1988-07-25 | 1992-05-05 | Siegfried K. Peter | Process for the recovery of monoglycerides and diglycerides from a mixture containing monoglycerides, diglycerides, and triglycerides |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8567412B2 (en) | 1997-12-24 | 2013-10-29 | Biosyntec | Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters |
US20060213533A1 (en) * | 1997-12-24 | 2006-09-28 | Imam Emami | Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters |
US20040026318A1 (en) * | 2000-06-22 | 2004-02-12 | Lemaire Benoit | Method for fractionating essential oils using at least a fluorinated solvent |
US6942881B2 (en) | 2000-08-24 | 2005-09-13 | Chr. Hansen A/S | Purification process for improving total yield of curcuminoid coloring agent |
US20030180401A1 (en) * | 2000-08-24 | 2003-09-25 | Chr. Hansen A/S | Purification process for improving total yield of curcuminoid colouring agent |
US6576273B2 (en) * | 2000-08-24 | 2003-06-10 | Chr. Hansen A/S | Purification process for improving total yield of curcuminoid colouring agent |
US20030099565A1 (en) * | 2001-10-12 | 2003-05-29 | Korea Institute Of Science And Technology | Method for removing waxes from molded part in powder injection molding by using mixed fluid |
US20040131748A1 (en) * | 2002-11-12 | 2004-07-08 | Water Solutions, Inc. | Process for extracting carotenoids from fruit and vegetable processing waste |
US7138152B2 (en) | 2002-11-12 | 2006-11-21 | Water Solutions, Inc. | Process for extracting carotenoids from fruit and vegetable processing waste |
US20070071861A1 (en) * | 2002-11-12 | 2007-03-29 | Water Solutions, Inc. | Process for extracting carotenoids from fruit and vegetable processing waste |
US7527820B2 (en) | 2002-11-12 | 2009-05-05 | Water Solutions, Inc. | Composition resulting from process for extracting carotenoids from fruit and vegetable processing waste |
US20040191384A1 (en) * | 2003-03-25 | 2004-09-30 | Naik Jarpla Pura | Process for the preparation of colorant from oleoresin |
US7501141B2 (en) * | 2003-03-25 | 2009-03-10 | Council Of Scientific And Industrial Research | Process for the preparation of colorant from oleoresin |
US20060252949A1 (en) * | 2003-09-25 | 2006-11-09 | Lalit Chordia | Recovery of residual specialty oil |
EP1986756A1 (en) * | 2006-02-07 | 2008-11-05 | Industrial Research Limited | Near-critical fluid extraction process |
US20100151098A1 (en) * | 2006-02-07 | 2010-06-17 | Industrial Research Limited | Near-critical fluid extraction process |
EP1986756A4 (en) * | 2006-02-07 | 2010-07-21 | Ind Res Ltd | PROCESS FOR EXTRACTION WITH NEARLY CRITICAL FLUID |
US8580116B2 (en) | 2006-02-07 | 2013-11-12 | Industrial Research Limited | Near-critical fluid extraction process |
FR2905284A1 (fr) * | 2006-08-29 | 2008-03-07 | Nat Invo Sarl | Procede d'extraction d'une substance d'un materiau. |
US20080233238A1 (en) * | 2007-02-08 | 2008-09-25 | Grimmway Enterprises, Inc. | Supercritical co2 carrot feedstock extraction |
US8398857B2 (en) | 2009-10-22 | 2013-03-19 | Epic Oil Extractors, Llc | Extraction of solute from solute-bearing material |
US20110094961A1 (en) * | 2009-10-22 | 2011-04-28 | Epic Oil Extractors, Llc | Extraction of solute from solute-bearing material |
WO2011060170A1 (en) * | 2009-11-11 | 2011-05-19 | Dynasep Llc | Energy efficient acetone drying method |
US8415506B2 (en) | 2009-11-11 | 2013-04-09 | Dynasep Inc. | Energy efficient acetone drying method |
US20110112329A1 (en) * | 2009-11-11 | 2011-05-12 | Dynasep Llc | Energy efficient acetone drying method |
EP2428258A1 (en) * | 2010-05-31 | 2012-03-14 | China Agricultural University | Process for extracting plant-derived natural products with polarity or intermediate polarity |
EP2428258B1 (en) * | 2010-05-31 | 2017-03-29 | China Agricultural University | Process for extracting plant-derived natural products with polarity or intermediate polarity |
US9132363B2 (en) | 2012-11-20 | 2015-09-15 | Apeks Llc | Extraction system |
US9908062B2 (en) | 2012-11-20 | 2018-03-06 | Andrew Paul Joseph | Extraction apparatus and method |
US9908063B2 (en) | 2012-11-20 | 2018-03-06 | Andrew Paul Joseph | Extraction apparatus |
CN108288738A (zh) * | 2018-01-30 | 2018-07-17 | 常州大学 | 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法 |
CN108288738B (zh) * | 2018-01-30 | 2021-03-23 | 常州大学 | 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法 |
Also Published As
Publication number | Publication date |
---|---|
CA2250051A1 (en) | 1998-07-30 |
ATE285242T1 (de) | 2005-01-15 |
EP0917876A1 (en) | 1999-05-26 |
DE69732031D1 (de) | 2005-01-27 |
EP0917876B1 (en) | 2004-12-22 |
WO1998032449A1 (es) | 1998-07-30 |
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Owner name: ASOCIACION DE INVETIGACION DEL LA INDUSTRIA AGROAL Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PIQUER, MIGUEL BLASCO;FERRI, BAUTISTA ENRIQUE MIRA;FUE, JUAN GABRIEL MARTINEZ;AND OTHERS;REEL/FRAME:009465/0468;SIGNING DATES FROM 19980831 TO 19980911 |
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